Upper Matecumbe Key Travel Guide

Tourist Guide

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
A pier extending into calm waters with a covered seating area and a sandy beach.
A pelican standing on a wooden dock.
A pier with birds perched on poles, a sign, and a bridge in the background.
A calm lake with a reflection of trees and a cloudy sky.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is £171 per night from 29 Sept to 30 Sept
£171
29 Sept - 30 Sept
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is £160 per night from 18 Oct to 19 Oct
£160
18 Oct - 19 Oct
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,782 reviews)
"Everything about the Chesapeake resort is perfect ,had the most incredible time ,will definitely return !!!"

Reviewed on 17 Sept 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is £172 per night from 27 Sept to 28 Sept
£172
27 Sept - 28 Sept
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
Amara Cay Resort
See all 2,748 properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
Breezy Palms Resort
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

Islamorada FL
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Lorelei Restaurant & Cabana Bar and Keys ...
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Oceanfront Private Cottage!

Oceanfront Private Cottage!

Islamorada FL
Stay at this cottage in Islamorada. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
10/10 Exceptional! (119 reviews)
"Beautiful home!! Had everything we needed for our 7 night stay. We will definitely be back."

Reviewed on 23 Aug 2026

Oceanfront Private Cottage!
See all properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
See properties

Cities near Upper Matecumbe Key

A beach with palm trees and white lounge chairs under a clear blue sky.

Islamorada

Explore a world of travel with Expedia